76469-88-0

6908-41-4

151-50-8

76469-88-0

Methyl 4-(hydroxymethyl)benzoate (1.00 g) was dissolved in dichloromethane (20 mL). To this solution was added triethylamine (0.9 mL), followed by the slow dropwise addition of a dichloromethane solution of methanesulfonyl chloride (0.70 g) (dichloromethane: 5 mL) under ice bath cooling. The reaction mixture was stirred for 15 h at room temperature, then diluted with dichloromethane, washed sequentially with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was dissolved in acetonitrile (12 mL). Potassium cyanide (0.80 g) and 18-crown-6 (0.16 g) were added and the mixture was stirred at room temperature for 40 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and the residue was diluted with dichloromethane, washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation again under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane) to give a colorless crystalline product (0.91 g, 86% yield). A portion of the product was recrystallized from a solvent mixture of hexane and ethyl acetate to give colorless crystals. The product was characterized by 1H-NMR (CDCl3): δ 3.82 (2H, s), 3.93 (3H, s), 7.42 (2H, d, J = 8.3 Hz), 8.06 (2H, d, J = 8.3 Hz).